Literature DB >> 21200910

4,4'-Bis(acetyl-amino)-1,1'-ethyl-enedipyridinium bis-(tetra-fluorido-borate).

Jiang-Sheng Li, Wei-Dong Liu, Dao-Wu Yang.   

Abstract

In the organic cation of the title compound, C(16)H(20)N(4)O(2) (2+)·2BF(4) (-), the pyridinium rings are nearly parallel, with a dihedral angle of 12.54 (12)°. The crystal packing is stabilized by N-H⋯F, C-H⋯F and C-H⋯O hydrogen bonds.

Entities:  

Year:  2007        PMID： 21200910      PMCID： PMC2914995          DOI： 10.1107/S1600536807062617

Source DB:  PubMed          Journal:  Acta Crystallogr Sect E Struct Rep Online        ISSN： 1600-5368


Related literature

For the 1,2-bis­(amino­pyridinium)ethane dication, see: Xu et al. (2007 ▶); Fan et al. (2007 ▶). For related literature, see: Allen et al. (1987 ▶); Li (2007 ▶); Loeb & Wisner (1998 ▶).

Experimental

Crystal data

C16H20N4O2 2+·2BF4 − M = 473.98 Monoclinic, a = 11.368 (2) Å b = 19.422 (4) Å c = 9.0959 (18) Å β = 101.12 (3)° V = 1970.6 (7) Å3 Z = 4 Mo Kα radiation μ = 0.16 mm−1 T = 113 (2) K 0.32 × 0.20 × 0.18 mm

Data collection

Rigaku Saturn diffractometer Absorption correction: multi-scan (CrystalClear; Rigaku/MSC, 2005 ▶) T min = 0.952, T max = 0.973 21399 measured reflections 3846 independent reflections 3138 reflections with I > 2σ(I) R int = 0.054

Refinement

R[F 2 > 2σ(F 2)] = 0.046 wR(F 2) = 0.144 S = 1.15 3846 reflections 299 parameters H atoms treated by a mixture of independent and constrained refinement Δρmax = 0.33 e Å−3 Δρmin = −0.30 e Å−3 Data collection: CrystalClear (Rigaku/MSC, 2005 ▶); cell refinement: CrystalClear; data reduction: CrystalClear; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997 ▶); molecular graphics: SHELXTL (Bruker, 1997 ▶); software used to prepare material for publication: CrystalStructure (Rigaku/MSC, 2005 ▶). Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536807062617/bt2653sup1.cif Structure factors: contains datablocks I. DOI: 10.1107/S1600536807062617/bt2653Isup2.hkl Additional supplementary materials: crystallographic information; 3D view; checkCIF report
C16H20N4O22+·2BF4–F000 = 968
Mr = 473.98Dx = 1.598 Mg m−3
Monoclinic, P21/cMo Kα radiation λ = 0.71073 Å
Hall symbol: -P 2ybcCell parameters from 4669 reflections
a = 11.368 (2) Åθ = 2.5–25.0º
b = 19.422 (4) ŵ = 0.16 mm−1
c = 9.0959 (18) ÅT = 113 (2) K
β = 101.12 (3)ºPrism, colorless
V = 1970.6 (7) Å30.32 × 0.20 × 0.18 mm
Z = 4
Rigaku Saturn diffractometer3846 independent reflections
Radiation source: Rotating anode3138 reflections with I > 2σ(I)
Monochromator: confocalRint = 0.054
Detector resolution: 7.31 pixels mm-1θmax = 26.0º
T = 113(2) Kθmin = 1.8º
ω scansh = −14→13
Absorption correction: multi-scan(CrystalClear; Rigaku/MSC, 2005)k = −23→23
Tmin = 0.952, Tmax = 0.973l = −11→11
21399 measured reflections
Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.046H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.144  w = 1/[σ2(Fo2) + (0.0635P)2 + 1.1885P] where P = (Fo2 + 2Fc2)/3
S = 1.15(Δ/σ)max < 0.001
3846 reflectionsΔρmax = 0.33 e Å−3
299 parametersΔρmin = −0.30 e Å−3
Primary atom site location: structure-invariant direct methodsExtinction correction: none
Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s. planes.
Refinement. Refinement of F2 against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F2, conventional R-factors R are based on F, with F set to zero for negative F2. The threshold expression of F2 > σ(F2) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F2 are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger.
xyzUiso*/Ueq
N10.32100 (17)0.51691 (10)0.6784 (2)0.0170 (4)
N20.56501 (18)0.63875 (11)0.9608 (2)0.0198 (5)
N30.15074 (17)0.44990 (10)0.3099 (2)0.0185 (4)
N4−0.11675 (18)0.34400 (11)0.0245 (2)0.0193 (5)
O10.72991 (16)0.57022 (9)1.0292 (2)0.0329 (5)
O2−0.23344 (15)0.42922 (9)−0.09946 (19)0.0256 (4)
C10.2934 (2)0.58226 (12)0.7114 (3)0.0189 (5)
H10.21720.60070.66850.023*
C20.3735 (2)0.62158 (12)0.8049 (3)0.0191 (5)
H20.35250.66720.82750.023*
C30.4868 (2)0.59555 (12)0.8686 (2)0.0165 (5)
C40.5144 (2)0.52784 (12)0.8323 (2)0.0182 (5)
H40.59020.50820.87280.022*
C50.4291 (2)0.49065 (12)0.7369 (2)0.0176 (5)
H50.44730.44490.71170.021*
C60.6832 (2)0.62699 (13)1.0264 (3)0.0214 (5)
C70.7466 (2)0.69017 (13)1.0942 (3)0.0261 (6)
H7A0.83070.67911.13500.039*
H7B0.70820.70701.17490.039*
H7C0.74260.72591.01720.039*
C80.2312 (2)0.47529 (12)0.5753 (2)0.0181 (5)
H8A0.14930.48930.58480.022*
H8B0.24150.42590.60190.022*
C90.2478 (2)0.48615 (13)0.4140 (3)0.0215 (5)
H9A0.24530.53600.39040.026*
H9B0.32670.46800.40200.026*
C100.0551 (2)0.48478 (13)0.2363 (3)0.0192 (5)
H100.05090.53310.25120.023*
C11−0.0370 (2)0.45266 (12)0.1399 (3)0.0182 (5)
H11−0.10390.47830.08930.022*
C12−0.0302 (2)0.38156 (12)0.1180 (2)0.0179 (5)
C130.0700 (2)0.34627 (13)0.1969 (3)0.0206 (5)
H130.07670.29800.18430.025*
C140.1577 (2)0.38076 (13)0.2913 (3)0.0217 (5)
H140.22470.35620.34490.026*
C15−0.2133 (2)0.36836 (13)−0.0805 (3)0.0203 (5)
C16−0.2881 (2)0.31331 (14)−0.1681 (3)0.0276 (6)
H16A−0.37160.3287−0.19380.041*
H16B−0.28340.2713−0.10770.041*
H16C−0.25810.3039−0.26020.041*
B10.0229 (2)0.65645 (12)0.4308 (3)0.0138 (5)
B20.5204 (3)0.83160 (14)0.9965 (3)0.0203 (6)
F10.02861 (13)0.59066 (7)0.49479 (16)0.0253 (4)
F2−0.09234 (14)0.68388 (8)0.43197 (18)0.0347 (4)
F30.03702 (16)0.65177 (9)0.28453 (19)0.0407 (5)
F40.10691 (17)0.69772 (9)0.5142 (2)0.0533 (6)
F50.44339 (13)0.88840 (7)0.97263 (16)0.0284 (4)
F60.60218 (15)0.83575 (8)0.90042 (18)0.0344 (4)
F70.45540 (13)0.77098 (7)0.96911 (17)0.0289 (4)
F80.58269 (13)0.83141 (8)1.14353 (17)0.0337 (4)
H4A−0.110 (2)0.3030 (16)0.024 (3)0.025 (8)*
H2A0.541 (2)0.6827 (15)0.963 (3)0.026 (7)*
U11U22U33U12U13U23
N10.0198 (10)0.0167 (10)0.0145 (9)−0.0025 (8)0.0037 (8)0.0001 (8)
N20.0203 (11)0.0165 (11)0.0206 (10)−0.0009 (9)−0.0008 (8)−0.0030 (8)
N30.0212 (10)0.0190 (10)0.0152 (9)−0.0043 (9)0.0031 (8)−0.0012 (8)
N40.0209 (11)0.0158 (11)0.0191 (10)−0.0011 (9)−0.0017 (8)−0.0017 (8)
O10.0231 (10)0.0234 (10)0.0467 (12)0.0029 (8)−0.0072 (9)−0.0055 (9)
O20.0256 (10)0.0233 (10)0.0242 (9)0.0037 (8)−0.0043 (7)0.0023 (7)
C10.0191 (12)0.0186 (12)0.0191 (11)0.0012 (10)0.0041 (9)0.0013 (9)
C20.0226 (13)0.0157 (12)0.0192 (12)0.0017 (10)0.0050 (10)−0.0010 (9)
C30.0164 (12)0.0194 (12)0.0135 (11)−0.0040 (10)0.0020 (9)−0.0001 (9)
C40.0188 (12)0.0192 (12)0.0160 (11)0.0006 (10)0.0017 (9)0.0019 (9)
C50.0199 (12)0.0159 (11)0.0173 (11)0.0013 (10)0.0043 (9)0.0009 (9)
C60.0217 (13)0.0215 (13)0.0194 (12)−0.0034 (11)0.0000 (10)0.0002 (10)
C70.0209 (13)0.0249 (14)0.0287 (14)−0.0047 (11)−0.0047 (11)−0.0040 (11)
C80.0162 (12)0.0192 (12)0.0168 (11)−0.0049 (10)−0.0015 (9)−0.0003 (9)
C90.0226 (13)0.0237 (13)0.0171 (12)−0.0070 (10)0.0010 (10)−0.0028 (10)
C100.0231 (13)0.0192 (12)0.0159 (11)0.0005 (10)0.0051 (10)0.0012 (9)
C110.0193 (12)0.0187 (12)0.0166 (11)−0.0007 (10)0.0033 (9)0.0005 (9)
C120.0181 (12)0.0209 (12)0.0152 (11)−0.0029 (10)0.0043 (9)−0.0006 (9)
C130.0202 (13)0.0193 (12)0.0212 (12)0.0020 (10)0.0014 (10)−0.0024 (9)
C140.0209 (13)0.0225 (13)0.0206 (12)0.0030 (10)0.0014 (10)−0.0006 (10)
C150.0189 (12)0.0254 (14)0.0166 (11)−0.0012 (10)0.0033 (10)0.0008 (10)
C160.0266 (14)0.0269 (14)0.0249 (13)−0.0052 (11)−0.0062 (11)0.0008 (11)
B10.0190 (13)0.0070 (12)0.0138 (12)0.0019 (10)−0.0013 (10)0.0015 (9)
B20.0228 (14)0.0180 (14)0.0208 (13)−0.0001 (11)0.0058 (11)0.0009 (11)
F10.0282 (8)0.0186 (7)0.0283 (8)0.0002 (6)0.0031 (6)0.0028 (6)
F20.0340 (9)0.0373 (9)0.0337 (9)0.0130 (7)0.0087 (7)0.0055 (7)
F30.0468 (10)0.0440 (10)0.0365 (9)0.0125 (8)0.0209 (8)0.0144 (8)
F40.0494 (11)0.0233 (9)0.0726 (14)−0.0099 (8)−0.0250 (10)0.0009 (8)
F50.0339 (9)0.0204 (8)0.0316 (8)0.0070 (6)0.0081 (7)−0.0004 (6)
F60.0409 (10)0.0280 (9)0.0403 (9)0.0029 (7)0.0231 (8)0.0036 (7)
F70.0277 (8)0.0187 (8)0.0374 (9)−0.0036 (6)−0.0004 (7)0.0015 (6)
F80.0268 (8)0.0462 (10)0.0257 (8)0.0029 (7)−0.0010 (6)−0.0096 (7)
N1—C51.342 (3)C8—C91.529 (3)
N1—C11.355 (3)C8—H8A0.9900
N1—C81.485 (3)C8—H8B0.9900
N2—C61.380 (3)C9—H9A0.9900
N2—C31.382 (3)C9—H9B0.9900
N2—H2A0.90 (3)C10—C111.378 (3)
N3—C101.345 (3)C10—H100.9500
N3—C141.358 (3)C11—C121.400 (3)
N3—C91.485 (3)C11—H110.9500
N4—C121.379 (3)C12—C131.403 (3)
N4—C151.391 (3)C13—C141.360 (3)
N4—H4A0.80 (3)C13—H130.9500
O1—C61.222 (3)C14—H140.9500
O2—C151.210 (3)C15—C161.496 (3)
C1—C21.355 (3)C16—H16A0.9800
C1—H10.9500C16—H16B0.9800
C2—C31.401 (3)C16—H16C0.9800
C2—H20.9500B1—F41.361 (3)
C3—C41.406 (3)B1—F31.373 (3)
C4—C51.375 (3)B1—F11.401 (3)
C4—H40.9500B1—F21.416 (3)
C5—H50.9500B2—F71.387 (3)
C6—C71.495 (3)B2—F81.387 (3)
C7—H7A0.9800B2—F61.396 (3)
C7—H7B0.9800B2—F51.399 (3)
C7—H7C0.9800
C5—N1—C1120.1 (2)N3—C9—C8109.43 (19)
C5—N1—C8120.6 (2)N3—C9—H9A109.8
C1—N1—C8119.3 (2)C8—C9—H9A109.8
C6—N2—C3128.4 (2)N3—C9—H9B109.8
C6—N2—H2A114.9 (18)C8—C9—H9B109.8
C3—N2—H2A115.4 (18)H9A—C9—H9B108.2
C10—N3—C14119.8 (2)N3—C10—C11122.1 (2)
C10—N3—C9120.6 (2)N3—C10—H10119.0
C14—N3—C9119.6 (2)C11—C10—H10119.0
C12—N4—C15128.2 (2)C10—C11—C12118.7 (2)
C12—N4—H4A118 (2)C10—C11—H11120.6
C15—N4—H4A114 (2)C12—C11—H11120.6
N1—C1—C2120.7 (2)N4—C12—C11123.9 (2)
N1—C1—H1119.6N4—C12—C13118.0 (2)
C2—C1—H1119.6C11—C12—C13118.1 (2)
C1—C2—C3120.6 (2)C14—C13—C12120.4 (2)
C1—C2—H2119.7C14—C13—H13119.8
C3—C2—H2119.7C12—C13—H13119.8
N2—C3—C2117.7 (2)N3—C14—C13120.8 (2)
N2—C3—C4124.3 (2)N3—C14—H14119.6
C2—C3—C4118.0 (2)C13—C14—H14119.6
C5—C4—C3118.5 (2)O2—C15—N4122.2 (2)
C5—C4—H4120.7O2—C15—C16123.3 (2)
C3—C4—H4120.7N4—C15—C16114.5 (2)
N1—C5—C4122.1 (2)C15—C16—H16A109.5
N1—C5—H5119.0C15—C16—H16B109.5
C4—C5—H5119.0H16A—C16—H16B109.5
O1—C6—N2122.8 (2)C15—C16—H16C109.5
O1—C6—C7124.0 (2)H16A—C16—H16C109.5
N2—C6—C7113.2 (2)H16B—C16—H16C109.5
C6—C7—H7A109.5F4—B1—F3112.2 (2)
C6—C7—H7B109.5F4—B1—F1109.50 (19)
H7A—C7—H7B109.5F3—B1—F1109.73 (19)
C6—C7—H7C109.5F4—B1—F2109.0 (2)
H7A—C7—H7C109.5F3—B1—F2108.29 (19)
H7B—C7—H7C109.5F1—B1—F2108.0 (2)
N1—C8—C9109.54 (19)F7—B2—F8109.0 (2)
N1—C8—H8A109.8F7—B2—F6109.4 (2)
C9—C8—H8A109.8F8—B2—F6109.0 (2)
N1—C8—H8B109.8F7—B2—F5110.2 (2)
C9—C8—H8B109.8F8—B2—F5109.9 (2)
H8A—C8—H8B108.2F6—B2—F5109.2 (2)
C5—N1—C1—C2−0.9 (3)C14—N3—C9—C8−78.7 (3)
C8—N1—C1—C2−179.9 (2)N1—C8—C9—N3−174.58 (18)
N1—C1—C2—C30.5 (4)C14—N3—C10—C11−0.7 (3)
C6—N2—C3—C2−174.5 (2)C9—N3—C10—C11−179.4 (2)
C6—N2—C3—C44.2 (4)N3—C10—C11—C12−0.2 (3)
C1—C2—C3—N2178.8 (2)C15—N4—C12—C1111.1 (4)
C1—C2—C3—C40.0 (3)C15—N4—C12—C13−169.5 (2)
N2—C3—C4—C5−178.8 (2)C10—C11—C12—N4−179.9 (2)
C2—C3—C4—C5−0.1 (3)C10—C11—C12—C130.6 (3)
C1—N1—C5—C40.7 (3)N4—C12—C13—C14−179.6 (2)
C8—N1—C5—C4179.8 (2)C11—C12—C13—C14−0.2 (4)
C3—C4—C5—N1−0.2 (3)C10—N3—C14—C131.2 (3)
C3—N2—C6—O1−11.9 (4)C9—N3—C14—C13179.9 (2)
C3—N2—C6—C7168.7 (2)C12—C13—C14—N3−0.7 (4)
C5—N1—C8—C9−89.3 (3)C12—N4—C15—O2−1.4 (4)
C1—N1—C8—C989.7 (3)C12—N4—C15—C16177.8 (2)
C10—N3—C9—C8100.0 (2)
D—H···AD—HH···AD···AD—H···A
N2—H2A···F70.90 (3)1.98 (3)2.862 (3)168 (3)
N4—H4A···F4i0.80 (3)2.08 (3)2.868 (3)170 (3)
C1—H1···F10.952.413.269 (3)150
C1—H1···F40.952.533.358 (3)145
C4—H4···O2ii0.952.503.404 (3)159
C5—H5···F6iii0.952.373.251 (3)153
C10—H10···F30.952.333.285 (3)179
C11—H11···O1iv0.952.583.496 (3)162
C13—H13···F2i0.952.483.391 (3)162
C14—H14···F8iii0.952.223.050 (3)145
Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯AD—HH⋯AD⋯AD—H⋯A
N2—H2A⋯F70.90 (3)1.98 (3)2.862 (3)168 (3)
N4—H4A⋯F4i0.80 (3)2.08 (3)2.868 (3)170 (3)
C1—H1⋯F10.952.413.269 (3)150
C1—H1⋯F40.952.533.358 (3)145
C4—H4⋯O2ii0.952.503.404 (3)159
C5—H5⋯F6iii0.952.373.251 (3)153
C10—H10⋯F30.952.333.285 (3)179
C11—H11⋯O1iv0.952.583.496 (3)162
C13—H13⋯F2i0.952.483.391 (3)162
C14—H14⋯F8iii0.952.223.050 (3)145

Symmetry codes: (i) ; (ii) ; (iii) ; (iv) .

  1 in total

1.  2,2'-Ethyl-enediisoquinolinium dibromide dihydrate.

Authors:  Jiang-Sheng Li; Peng-Yu Li
Journal:  Acta Crystallogr Sect E Struct Rep Online       Date:  2009-10-31
  1 in total

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